Back in late April, Thomas, Levi & I visited Nantucket for the first time with our good friends to attend the Daffodil Festival. We also had another agenda while we were there – little to my friend’s knowledge at the time, until her new FIANCÉ popped the question over the weekend! It was such an exciting moment to witness and made our trip that much better with endless celebration. Not gonna lie, I was so worried I’d accidentally reveal the plan on the Thursday and Friday leading up to the Saturday am proposal. Beyond relieved to have been able to keep my lips buttoned up to that point hahah.
Although we weren’t in Nantucket longer than 4 days, I did a poll on Instagram to see whether or not a travel guide would be helpful to post about. Clearly, majority ruled YES otherwise I wouldn’t have taken the hours to write this up. So keep in mind, we packed a lot into our time here and still didn’t get to see/do everything available on the Island – but all the more reason to visit again & to add onto this post over time!
A custom bottle I had painted by the beyond talented Ashley of Bespoke Bubbly for the newly engaged couple
Nantucket hosts a variety of events on the island each year, with three described as borderline festivals with the turnout of attendees it often attracts.
In April, there’s the Daffodil “Daffy” Festival which we attended for the first time ever ourselves, as well as it happened to be the first time in 2 years since COVID when it was held. As you can imagine, the enthusiasm and excitement was next level.
In May, there’s Figawi Race Weekend which consists of 2 days of sailing/racing on Nantucket Sound.
And in December, there’s the Nantucket Christmas Stroll which is essentially a celebration of all things holiday on the island.
How To Get There
Because we were traveling with the dogs, we took the 2-hour car ferry from Hyannis, MA but there’s a quicker 1-hour ferry ride that operates out of the same terminal/landing if you’re not planning to bring your car. It made sense for us to have it for this particular weekend, but you can easily bike the island or get (overpriced) Ubers should you wish to explore outside of the downtown area more frequently. The Seastreak ferry also operates a ride to the island out of New Bedford, should you be closer to that terminal than the Hyannis port.
WHERE WE STAYED
We stayed in this beautifully-decorated boutique hotel that was literally 2 minutes walking distance from the ferry terminal AND pet-friendly! Offering only 20 rooms and a delicious restaurant/bar scene on the lobby level, we absolutely lucked out with staying here during our first Nantucket trip. It really set the bar high for us & all our future trips to the Island.
I didn’t get a photo of our room unfortunately but you can take a peek at what some of the guest suites look like here. We personally LOVED our enormous shower with what appeared to be hand-painted tilework from floor to ceiling. It was a little loud at times, due to it being an older building with thin walls, but we got used to it after the first night. Nothing like what it used to be when we lived in NYC though! Plus the location and amenities were enormous pros that the limited noise level was very easy to overlook in the grand scheme of things.
THINGS TO DO
Visit The Lighthouses
There are (3) lighthouses to visit on Nantucket: Sankaty Head Light, Brant Point & Great Point. The first can be visited during your drive to ‘Sconset and Brant Point is within walking distance from the downtown area – it’s the first lighthouse/structure seen as you approach the island by ferry. Great Point is located at the far North tip of Nantucket that can only be reached (realistically) by car on the beach. You’ll have to ensure your car has the proper decal sticker in order to enter the park, as well as know how to properly release air from your tires so you don’t get stuck out there. But apparently it’s worth the adventure to see it!
Rustic brewery for live music, tastings & tours along with 3 bars serving craft beer, wine & drinks. We went here 2x during our trip and had so much fun. Dog-friendly space with food trucks offering plenty of options. It’s definitely a popular place that most people spend a majority of their day at. I suggest getting there right at opening hour so you’re one of the first in line to enter. Sometimes there’s a cover fee, so be prepared to bring some cash. We didn’t go on the tour but heard amazing things about it, so take advantage if you have the chance to do it!
To get there, you can hop on the free shuttle (aka van) that makes trips to-from the brewery every 20 minutes. It picks up/drops off passengers at the corner of Federal & E Chestnut Streets, right in front of the Nantucket Information Bureau. The driver works on tips, so be sure to bring extra cash for that as well. I personally think it’s the best (& safest) way to get there, given the limited parking right onsite can get crowded & competitive. There is a larger lot 200 yards down the road you can park in should you choose to drive, but you’ll have to walk along the road path back to the Brewery entrance.
Down the street from the brewery is this low-key, rustic sand beach on the Atlantic side with waves attracting surfers & bodyboarders. Definitely a place to check out when the weather permits.
Located in the heart of downtown, the Whaling Museum offers guests the perfect mix of modern design combined with history and tradition. Featuring permanent and rotating exhibitions in 9 galleries, with over a thousand works of art, artifacts and treasures on display, it tells the Island’s fascinating stories over 4 centuries. The museum is home to a 46-foot sperm whale skeleton, a massive Fresnel lens, a restored 1847 candle factory and a relaxing, fully-accessible rooftop deck offers stunning views of Nantucket harbor (as per the website.)
If you’re looking to get out of the downtown area for a quieter taste of Nantucket, then here’s where to find it. In this charming residential neighborhood of Siasconset Old Historic District about ~20 min from town, you’ll walk a footpath that runs through the backyards of gorgeous homes along with bluff overlooking scenic sea & heathland views.
Some big retailers like The Black Dog, Vineyard Vines, Faherty & Southern Tide have specific Nantucket attire you can’t find elsewhere. But I personally would check out some of the small boutiques the Island has to offer. Here are some of our favorites:
Gift shop offering high-quality, Nantucket-inspired accessories, apparel, jewelry, home decor, stationery and art made up of mostly small makers and artists
Family owned clothing store since 1945 specializing in Nantucket Reds attire
Nantucket cottage-style home goods store with a selection of fine home furnishings, handwoven textiles, clothing, accessories and full-scale interior design services
Upscale women’s clothing boutique offering cashmere ruanas, jewelry, home decor & gifts
Classic Nantucket-inspired clothing & accessories
Best place to get “Nantucket” tees & sweatshirts
Women’s clothing boutique offering beachy, feminine, easy-to-wear pieces
Island boutique offering monogram jewelry, Nantucket charms, cashmere accessories & more
WHERE WE DRANK + DINED
Bright, brick-lined cafe with outdoor tables offering eclectic eats, coffees, smoothies & creative cocktails
Relaxed cafe offering familiar American classics, coffee, board games & books in a cozy hangout
A small marketplace environment with food products ranging from organic produce and baked goods to grab-and-go meals
An amazing spot for breakfast sandwiches & iced coffee. Located a bit outside of the main downtown stretch but worth the trip.
Country cafe serving house-made donuts (so good!) & simple American breakfast & lunch for more than 80 years – cash only*
Local go-to sandwich shop offering hearty sandwiches & chocolate chip cookies with picnic table dining available
Global fare in a chic atmosphere with a patio offering shared plates, salads & brunch, plus drinks. They have a great brunch menu and a fun patio bar outback that gets exciting after hours
Chill sports bar offering house-made BBQ plates & sides, plus Tennessee whiskeys & ample craft beers
Relaxed restaurant & bar serving locally sourced, globally influenced fare in a contemporary space *recommend making a reservation*
California-inspired fare in a restaurant attached to a retrofitted railway car that’s a lively bar
Unpretentious hangout for burgers, seafood & pub grub, plus sports TV & live music some nights
Low-key pub with nautical decor serving classic New England seafood dishes, plus weekend brunch
Via Mare at Greydon House
A whimsical take on the Venetian tradition of small plate dining & drinking in the spirited taverns known as bacari, Via Mare looks to Venezia’s long history as a central hub in the spice trades & adventurously follows these trade winds in curating their eclectic cuisine, wine & cocktail programs. In other words, it’s Italian-ish.
A focused menu of upscale American fare served in a small, simple space inside a shingled house. Also a bit out of the downtown neighborhood but delicious option for breakfast/brunch/lunch.
An adorable family-farm grocery store/market that serves incredible sandwiches and to-go options. Located near Cisco Brewery.
An eclectic menu of inventive seafood & meat dishes lures locals to this welcoming institution
Seasonal seafood standby serving burgers, sandwiches & cocktails in comfy digs